Catalyst-free Tandem 1,3-Dipolar Cycloaddition/Aldol Condensation: Diastereoselective Construction of the Azatetraquinane Skeleton

被引：9
|
作者：
Zimnitskiy, Nikolay S. [1 ]
Denikaev, Andrey D. [1 ]
Barkov, Alexey Y. [1 ]
Kutyashev, Igor B. [1 ]
Korotaev, Vladislav Y. [1 ]
Sosnovskikh, Vyacheslav Y. [1 ]
机构：
[1] Ural Fed Univ, Inst Nat Sci & Math, Ekaterinburg 620000, Russia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 13期
基金：
俄罗斯基础研究基金会;
关键词：
STABILIZED AZOMETHINE YLIDES; STEREOSELECTIVE-SYNTHESIS; NATURAL-PRODUCTS; CAGE COMPOUNDS; REGIO; NINHYDRIN; MULTICOMPONENT; CRINIPELLIN; DERIVATIVES; CURCUMIN;
D O I：
10.1021/acs.joc.0c01127
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The one-pot regioselective and diastereoselective method for the synthesis of 5-(het)aroyl-7-(het)-arylhexahydrobenzo[4,5]pentaleno[1,6a-b](thia)pyrrolizine-6,12-diones from accessible 1,5-di(het)arylpent-4-ene-1,3-diones or curcuminoids in 38-98% yield was developed. This reaction proceeds as a sequence of 1,3-dipolar cycloaddition of azomethine ylide generated in situ from ninhydrin and (thia)proline at the C=C bond of corresponding enedione, followed by spontaneous intramolecular aldol condensation and leads to the formation of an azatetraquinane scaffold.
引用
收藏
页码：8683 / 8694
页数：12
相关论文
共 50 条
  • [21] Multicomponent 1,3-Dipolar Cycloaddition Reactions in the Construction of Hybrid Spiroheterocycles
    Arumugam, Natarajan
    Kumar, Raju Suresh
    Almansour, Abdulrahman I.
    Perumal, Subbu
    CURRENT ORGANIC CHEMISTRY, 2013, 17 (18) : 1929 - 1956
  • [22] Enantio- and diastereoselective synthesis of isoxazolidines by asymmetric 1,3-dipolar cycloaddition of nitrones
    Ukaji, Y
    Taniguchi, K
    Sada, K
    Inomata, K
    CHEMISTRY LETTERS, 1997, (06) : 547 - 548
  • [23] Diastereoselective synthesis of pyrrolidines via 1,3-dipolar cycloaddition of a chiral azomethine ylide
    Karthikeyan, K.
    Kumar, R. Senthil
    Muralidharan, D.
    Perumal, P. T.
    TETRAHEDRON LETTERS, 2009, 50 (51) : 7175 - 7179
  • [24] Highly diastereoselective 1,3-dipolar cycloaddition via in situ formed ketimine ylides
    Cheng, Yu
    Liu, Ya-Nan
    Ye, Jia
    He, Long
    Kang, Tai-Ran
    Liu, Quan-Zhong
    TETRAHEDRON LETTERS, 2012, 53 (50) : 6775 - 6778
  • [25] Enantio- and Diastereoselective Synthesis of Isoxazolidines by Asymmetric 1,3-Dipolar Cycloaddition of Nitrones
    Ukaji, Y.
    Taniguchi, K.
    Sada, K.
    Inomata, K.
    Chemistry Letters, (06):
  • [26] A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition
    Anis'kov, Alexander
    Klochkova, Irina
    Tumskiy, Roman
    Yegorova, Alevtina
    MOLECULES, 2017, 22 (12):
  • [27] An efficient and diastereoselective intramolecular 1,3-dipolar cycloaddition of cyclic azomethine ylides and nitrones
    Pedrosa, Rafael
    Andres, Celia
    Nieto, Javier
    Perez-Cuadrado, Cristobal
    San Francisco, Ivan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (14) : 3259 - 3265
  • [28] Highly efficient and diastereoselective construction of substituted pyrrolidines bearing a quaternary carbon center via 1,3-dipolar cycloaddition
    Wang, Kai-Kai
    Li, Yan-Li
    Xiao-Qian, Shuai
    Chen, Rongxiang
    Sun, Aili
    Wang, Zhan-Yong
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2022, 59 (09) : 1616 - 1625
  • [29] Gold nanoparticle as a Lewis acid catalyst in 1,3-dipolar cycloaddition reaction
    Yazdani, Hossein
    Pardis, Samira
    Loni, Masood
    Bazgir, Ayoob
    CATALYSIS COMMUNICATIONS, 2020, 134
  • [30] Zinc chloride doped natural phosphate as 1,3-dipolar cycloaddition catalyst
    Lazrek, HB
    Rochdi, A
    Kabbaj, Y
    Taourirte, M
    Sebti, S
    SYNTHETIC COMMUNICATIONS, 1999, 29 (06) : 1057 - 1063
12345